The Power of Two

They built Living Luxe side by side—as partners in business and in life. At this year’s Living Luxe Awards Show, Jennifer Lipkowitz and Anthony Sirianni stepped into an entirely new chapter together.

Anthony Sirianni remembers waking up suddenly in the middle of the night knowing exactly how he wanted to propose to Jennifer Lipkowitz at the Living Luxe Awards Show. It wouldn’t be subtle, and it certainly wouldn’t be private.

For Lipkowitz, publisher of Living Luxe, and Sirianni, co-founder and chief operating officer, the proposal could happen in only one place: at the centre of the world they had spent years building together.

Just days earlier, more than 5,000 guests had flocked to the opening night party of the Living Luxe Design Show. Packed runway shows unfolded alongside immersive installations and a sprawling cocktail party. Media outlets had already begun covering the show before it even opened its doors, and Conservative leader Pierre Poilievre made a surprise appearance to honour the trades. The atmosphere in the room felt electric.

“It generated so much hype,” Lipkowitz says. “I’ve honestly never seen the show hit that level of excitement or media attention before.” At some point amid the chaos of opening night, she knew Living Luxe had entered an entirely different chapter. What Lipkowitz didn’t realize yet was that, by the end of the weekend, so would her life.

When I call both of them for our interview, the energy is exactly what you would expect from two people simultaneously running a magazine, a media company, and a life together. What was originally meant to be an in-person interview at the office instead unravels into a phone call, with Lipkowitz calling out for Sirianni mid-conversation while getting ready for a photo shoot, half-jokingly warning him that if he doesn’t come to the phone soon, he’s going to miss his own cover story. There’s laughter and playful banter. At one point, Lipkowitz begins answering a question before Sirianni cuts in: “Don’t say ‘for us.’ That’s your opinion. I have my own.”

It’s chaotic in the way only long-term partnerships can be: two people who know each other well enough to finish each other’s thoughts, challenge each other mid-sentence, and somehow still land in the same place. And maybe that’s exactly why the company works. “Living Luxe is our relationship brought to life,” Sirianni says simply.

Part of that dynamic comes from how different they are. Lipkowitz describes Sirianni as deeply operational and detail-oriented, while she naturally gravitates toward sales and marketing. Over the years, both say they’ve learned to trust each other enough not to micromanage every decision.

Before Living Luxe existed, there was just a conversation beside a pool in Jamaica. The couple were on their first vacation together when Sirianni asked Lipkowitz a deceptively simple question: What’s your dream? “I want to create a high-end home decor magazine,” she told him.

“Living Luxe is our relationship brought to life.”

If they were going to do this, it couldn’t look like everything else already on the market. “I said, ‘I’m in, but it has to have lifestyle in it,’ ” he recalls. And he meant it. Three months into their relationship, Sirianni made what Lipkowitz still describes as one of the biggest leaps of faith of his life: he quit his stable senior-management job to help build the company from scratch.

“I remember saying to him, ‘Anthony, you’re a single dad. This is a huge amount of pressure,’ ” Lipkowitz says. “But he believed in me completely. Most people don’t leave their careers for someone else’s dream.”

Today, Living Luxe extends well beyond the pages of a magazine. Even the show itself was built from within: a small but mighty team backing a production most people would assume required an entire corporate machine. Sirianni is still in awe when he talks about it. “We really did it from the ground up,” he says.

Behind the glamour is a reality both of them speak about honestly: the pressure. “There’s late nights. Things fall apart. Things don’t get done,” Lipkowitz says. “You have to pivot constantly. Sometimes you’re dealing with problems at two or three in the morning.” Even with a team she describes as hardworking and deeply dedicated, there are moments when both of them have to step into unexpected roles. “No one’s going to love your business the way you do,” she says.

For all the spectacle surrounding the company today, the sense of community behind it remains genuine. Many clients have become close friends, and relationships built through the brand now extend far beyond business.

“He believed in me completely. Most people don’t leave their careers for someone else’s dream.”

It’s precisely what made the location of the proposal feel so symbolic. Earlier that year, Sirianni had casually tested the waters. “One day, how would you feel about getting engaged?” he remembers asking Lipkowitz. Her response was characteristically calm. “We’re not in a rush to get married,” she told him, “but I wouldn’t mind getting engaged.”

Months before the show, Sirianni quietly began planning the proposal in secret, no easy feat for someone who spends nearly every waking moment beside his partner. “We work together, we live together—we’re always together,” he says. “It was super hard to keep that kind of secret from Jen. I really had to act like nothing was going on.”

Lipkowitz, meanwhile, was blissfully unaware. “I was in pure work mode,” she says, laughing. “I just wanted to know who the four finalists were.” So when Sirianni suddenly began speaking about their relationship during the awards show, Lipkowitz admits she was mostly confused. “I remember thinking, ‘Okay…you want to talk about this now?’ ” she says.

Then he got down on one knee. “I was in shock. I had absolutely no clue,” Lipkowitz says. From the front row, the disbelief registered instantly across her face before the rest of the room fully caught up. Surrounded by family, friends, and many of the people who had been part of Living Luxe from the beginning, it was one of those rare moments that felt intimate and entirely public at the same time.

Neither of them pretends that balancing business and a relationship is easy. In fact, both admit they’re still figuring it out in real time. “We’re not balanced,” Sirianni says honestly. “It’s really hard to turn it off.” The challenge, Lipkowitz explains, is that when your business partner is also your life partner, disagreements don’t end when the workday does. “Ninety-five per cent of the time we get along and see eye-to-eye,” she says. “But the other five per cent? We’re both stubborn. We both want to win.” The line between work and life rarely stays clear for long, but date nights become intentional attempts not to talk about work at all.

Still, both say that years from now, when the late nights and constant pressure no longer feel quite so immediate, they’ll remember this chapter for something much simpler. “The love we share,” Sirianni says. “And the legacy.” He pauses. “These magazines, the words, the things we’ve created—they’re not going away. They’ll always be here. That makes me really proud.”